Synthesis of glycolurils and their analogues

• Published in: Russian chemical reviews 2018-01, Vol.87 (1), p.89-108
• Main Authors: Kravchenko, Angelina N., Baranov, Vladimir V., Gazieva, Galina A.
• Format: Article
• Language: English
• Subjects: Antibacterial materials; Carbonyl compounds; Dienes; Imidazole; Isocyanates; Organic chemistry; Ureas
• ISSN: 0036-021X; 1468-4837
• DOI: 10.1070/RCR4763

Glycolurils - tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-diones - have found widespread applications in various fields of science and technology. Among them, there are pharmacologically active compounds (antibacterial, nootropic, neurotropic agents, etc.), explosives, gelators, etc. They are used as building blocks in supramolecular chemistry. Therefore, the development of new methods for the synthesis of glycolurils and their analogues has constantly attracted the attention of researchers. In this review, we analyze various approaches to the synthesis of glycolurils and their analogues. The review covers both classical reactions of ureas and related compounds with α-dicarbonyl compounds or with 4,5-dihydroxyimida-zolidin-2-ones (-thiones) and their imino analogues and new original reactions of 4,5-dihydroxyimidazolidin-2-ones (-thiones), imidazolinones and their bicyclic analogues with ureas and KNCS in the presence of acids, condensations of 1,4-disubstituted 1,4-diaza-1,3-dienes with isocyanic and/or isothiocyanic acids or isocyanates, triazine ring contraction in imidazotriazines to give the imidazolidine ring, and transformations of urazoles. The bibliography includes 129 references.